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Cheap flights from Illinois to Anguilla from $380

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Anguilla departing on 7/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Illinois to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:00 am - 4:19 pm
ORD
-
AXA
10h 19m
1 stop
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$664American Airlines
Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
6:10 am - 4:19 pm
ORD
-
AXA
9h 09m
1 stop
American Airlines Logo
4:59 pm - 6:38 am
AXA
-
ORD
14h 39m
2 stops
$669American Airlines
Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
6:00 pm - 1:19 pm
ORD
-
AXA
18h 19m
1 stop
American Airlines Logo
4:55 pm - 12:19 am
AXA
-
ORD
8h 24m
1 stop
$724American Airlines
Mon, Jun 22 - Fri, Jun 26
American Airlines Logo
5:07 am - 4:19 pm
ORD
-
AXA
10h 12m
2 stops
American Airlines Logo
4:59 pm - 6:38 am
AXA
-
ORD
14h 39m
2 stops
$729American Airlines
Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
5:00 am - 4:15 pm
ORD
-
AXA
10h 15m
1 stop
American Airlines Logo
4:59 pm - 12:26 am
AXA
-
ORD
8h 27m
1 stop
$734American Airlines
Wed, Jun 24 - Sat, Jul 4
American Airlines Logo
5:10 am - 4:15 pm
ORD
-
AXA
10h 05m
2 stops
American Airlines Logo
12:40 pm - 11:39 pm
AXA
-
ORD
11h 59m
2 stops
$739American Airlines
Wed, Jun 24 - Sat, Jul 4
American Airlines Logo
5:59 pm - 1:11 pm
ORD
-
AXA
18h 12m
1 stop
American Airlines Logo
4:59 pm - 6:38 am
AXA
-
ORD
14h 39m
2 stops
$764American Airlines
Sat, Jul 25 - Sat, Aug 1
American Airlines Logo
5:00 am - 4:19 pm
ORD
-
AXA
10h 19m
1 stop
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$769American Airlines
Wed, Jul 22 - Sun, Jul 26
American Airlines Logo
5:07 am - 4:19 pm
ORD
-
AXA
10h 12m
2 stops
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$774American Airlines
Wed, Jul 22 - Sun, Jul 26
American Airlines Logo
5:07 am - 4:19 pm
ORD
-
AXA
10h 12m
2 stops
American Airlines Logo
4:59 pm - 6:38 am
AXA
-
ORD
14h 39m
2 stops
$799American Airlines
Sat, Jul 25 - Sat, Aug 1

American Airlines flights from Illinois to Anguilla

Our best American Airlines deals on Illinois to Anguilla flight tickets
American Airlines
Jul 7
ORD5:00 amChicago O'Hare Intl
10h 19m
1 stop
AXA4:19 pmThe Valley Wallblake Intl
Jul 22
AXA4:59 pmThe Valley Wallblake Intl
17h 09m
1 stop
ORD9:08 amChicago O'Hare Intl
$664
American Airlines
Jul 7
ORD6:10 amChicago O'Hare Intl
9h 09m
1 stop
AXA4:19 pmThe Valley Wallblake Intl
Jul 22
AXA4:59 pmThe Valley Wallblake Intl
14h 39m
2 stops
ORD6:38 amChicago O'Hare Intl
$669
American Airlines
Jun 22
ORD6:00 pmChicago O'Hare Intl
18h 19m
1 stop
AXA1:19 pmThe Valley Wallblake Intl
Jun 26
AXA4:55 pmThe Valley Wallblake Intl
8h 24m
1 stop
ORD12:19 amChicago O'Hare Intl
$724

JetBlue flights from Illinois to Anguilla

Our best JetBlue deals on Illinois to Anguilla flight tickets
JetBlue
Jul 30
ORD8:20 pmChicago O'Hare Intl
20h 15m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Aug 4
AXA9:46 amThe Valley Wallblake Intl
25h 20m
3 stops
ORD10:06 amChicago O'Hare Intl
$1,408
JetBlue
Jun 15
ORD8:20 pmChicago O'Hare Intl
20h 15m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Jun 19
AXA9:46 amThe Valley Wallblake Intl
28h 14m
3 stops
ORD1:00 pmChicago O'Hare Intl
$1,568
JetBlue
Jul 31
ORD8:20 pmChicago O'Hare Intl
20h 15m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Aug 4
AXA9:46 amThe Valley Wallblake Intl
25h 20m
3 stops
ORD10:06 amChicago O'Hare Intl
$1,658

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Anguilla that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 16, 2026.
Use the filters below to find and compare flights from Illinois to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

5:00 am-4:19 pm

1 stop10h 19m

The Valley Wallblake Intl

Wed 7/22

4:59 pm-9:08 am

1 stop17h 09m

$664

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

6:10 am-4:19 pm

1 stop9h 09m

The Valley Wallblake Intl

Wed 7/22

4:59 pm-6:38 am

2 stops14h 39m

$669

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 6/22

6:00 pm-1:19 pm

1 stop18h 19m

The Valley Wallblake Intl

Fri 6/26

4:55 pm-12:19 am

1 stop8h 24m

$724

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

5:07 am-4:19 pm

2 stops10h 12m

The Valley Wallblake Intl

Wed 7/22

4:59 pm-6:38 am

2 stops14h 39m

$729
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 6/24

5:00 am-4:15 pm

1 stop10h 15m

The Valley Wallblake Intl

Sat 7/4

4:59 pm-12:26 am

1 stop8h 27m

$734

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 6/24

5:10 am-4:15 pm

2 stops10h 05m

The Valley Wallblake Intl

Sat 7/4

12:40 pm-11:39 pm

2 stops11h 59m

$739

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/25

5:59 pm-1:11 pm

1 stop18h 12m

The Valley Wallblake Intl

Sat 8/1

4:59 pm-6:38 am

2 stops14h 39m

$764

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 7/22

5:00 am-4:19 pm

1 stop10h 19m

The Valley Wallblake Intl

Sun 7/26

4:59 pm-9:08 am

1 stop17h 09m

$769

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 7/22

5:07 am-4:19 pm

2 stops10h 12m

The Valley Wallblake Intl

Sun 7/26

4:59 pm-9:08 am

1 stop17h 09m

$774

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/25

5:07 am-4:19 pm

2 stops10h 12m

The Valley Wallblake Intl

Sat 8/1

4:59 pm-6:38 am

2 stops14h 39m

$799

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Anguilla from

How to get the cheapest flight ticket from Illinois to Anguilla

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Anguilla?

If you aren’t able to travel to Anguilla during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $0.

Cheap Illinois to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Anguilla

Fastest flight time

8h 27m

Direct flights

None
The fastest flight from Illinois to Anguilla takes 8h 27m
There are no direct flights from Illinois to Anguilla. There are no popular flight routes from Illinois to Anguilla.
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Frequently asked questions about flying from Illinois to Anguilla

  • When did momondo last update prices for flights from Illinois to Anguilla?

    Prices for flights from Illinois to Anguilla refresh daily.

  • How many operators does momondo search for flights from Illinois to Anguilla?

  • How old do you have to be to fly from Illinois to Anguilla?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Anguilla.

  • What documentation or ID do you need to fly to Anguilla?

    The required travel and health documents for your Anguilla trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Anguilla. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Anguilla

Compare and see reviews for airlines that fly from Illinois to Anguilla with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $529Free CancellationRating
7.1
11,662 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Anguilla?

It is quick and easy to find Illinois to Anguilla flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Anguilla that suits you.

Can I find flights from Illinois to Anguilla with flexible booking policies on momondo?

All flight searches from Illinois to Anguilla on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Illinois to Anguilla?

momondo provides multiple filters to help you find the best flight to Anguilla from Illinois. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Illinois to Anguilla right now. Can momondo alert me if prices change?

Price alerts on flights to Anguilla from Illinois are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo
Flights to The Valleyfrom $617